Jeremy and Elena
The relationship between adoptive brother and sister and biological cousins, Elena and Jeremy Gilbert has been a close, but often tense relationship. Jeremy was born two years after Elena was adopted by the Gray sons. They appeared to be very close until the night their parents died in a car accident. After that, Jeremy withdrew from the family and started using and selling drugs. She was concerned and angry about this and told Jeremy that she would either make him talk to someone in the family or else have him talk to a therapist. He replies that he doesn't want to do either. He finds some measure of happiness when he starts dating Vicki Donovan until she disappears one day, leaving Jeremy searching frantically for her. He finds her finally on the night of Halloween after she had been turned into a vampire. Elena tries to warn him to stay away from Vicki but he doesn't listen a nd almost gets killed by her when she can't reisist the blood urge. Later, after she was staked by Stefan and he was home, he tearfully asks Elena why "everyone had to die on him". Feeling horrible, Elena begs Stefan to erase his memories of her death and make him believe an alternate reality where Vicki was alive and okay, that she had left town and that he shouldn't be concerned because it was for the best. He believed this because of the compulsion he was under and told anyone who asked him that that was what he believed. Later, after reading her journal, and learning that he was under compulsion under her orders and she compared Vicki to a monster and revealed that she was worried about Jeremy. He angrily confronts her and tells her to go to hell and continues his antagonistic relationship with her throughout the rest of the season, and at one point getting into an altercation with Damon about it. He keeps things from his sister and doesn't tell her that Anna had given him her blood for him to take and that he was going to take his own life. Season 2 ''' When Elena goes into Jeremy's room after finding John on the ground, she anxiously runs into his room and anxiously shakes him awake until he suddenly wakes. She is concerned about him and asks Stefan if it was possible he was a vampire. Stefan shoots down that theory and tells him that Anna's blood healed him of any complications from the drugs. He is very disappinted that his suicide mission did not go off like he planned and gets reprimanded by Stefan, who tells him that the next time he tried that, it might actually work and to think before he did it. Later, he and Elena and Jenna go to the Lockwood's to mourn the loss of mayor Richard Lockwood who had died in the basement fire that Anna had died in along with many other tomb vampires. There, Jeremy meets Mason Lockwood for the first time. Later, Elena admits to Stefan that she does not want John in her life or Jeremy's life, mostly due to his negative view towards vampires and his inability to see things differently. Later, when Elena was kidnapped and taken to Elijah, Jeremy helped Bonnie get Elena back by using a tracking spell that called for the use of his blood. The effort worked and Stefan and Damon were able to track her down. Later, when Elena returned she and Jeremy greeted each other with big hugs. Later, when Stefan was trapped in the tomb after rescuing Jeremy form Katherine's clutches, Elena tried to leave the house to rescue him but was thwarted by Jeremy and Bonnie. Later, Elena and Jeremy both go to the Decade dance with their respective beu's. After Jenna's death by staking, Elena and Jeremy embrace after Jeremy tells her "I still have you" when Elena apologizes for the people he has lost in his life '''Season 3 During the summer after Stefan had left with Klaus, Jeremy was still struggling with the after effects of being brought back to life by Bonnie. Elena recognized that he was showing signs of trouble and tried to get to the bottom of it. She was dismayed to see him smoking at her birthday party and asked if Alaric could talk to him and knock some sense into him. During Ghost World, Elena was infuriated to discover that Anna was back as a ghost, using her foothold on Jeremy to come back. She angrily accused Anna of stealing the necklace that Bonnie needed in order to send the ghosts back. Anna denied having anything to do with the necklace's disappearance. During this time, Jeremy tearfully tells Elena that he could feel Anna, he could see her and that he knew it was wrong but he could sense her. He tells Elena that he had always loved ''her ''and that it had always been her. Elena tells him that everything he was feeling was in the past and that he couldn't love a ghost for the rest of his life. She tells Anna that he had the rest of his life ahead of him and that she was only holding him back. After Bonnie broke up with him and after losing Anna again, Jeremy starts to go downhill again, getting fired from his job and hanging out with Tyler Lockwood who had been sired by Klaus. After Jeremy is almost killed by Klaus, by being compelled to stand in front of a speeding car, Elena has Damon compel Jeremy to leave town and go to Denver to spend time with family friends until Klaus is gone.